Find cheap flights from Chicago O'Hare Airport to Caribbean Islands

Find cheap flights from Chicago O'Hare Airport to Caribbean Islands

Round-trip
Economy
Chicago (ORD)
Caribbean Islands
Tue 11/24
Tue 12/1
Any month
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Good to know

Low season

August Best time to beat the crowds with an average 4% drop in price.

High season

December Most popular time to fly with an average 15% increase in price.

Average price round-trip

$437 (avg. price over the last 2 weeks)

Good deal round-trip

$258 or less

Good deal one-way

$122 or less

Top tips for finding cheap flights to Caribbean Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean Islands is August.
  • Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean Islands flights

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Top 3 airlines serving Chicago O'Hare Intl to Caribbean Islands

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,287 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Coffee was super week No movies ORD-JFK"

Cons: "Tv dont work in a fly of 4hr 30 min"

Cons: "Was 2hrs behind schedule"

Cons: "This flight was very delayed"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

Pros: "JetBlue it have a lot more space for your and it was on time too but this morning the rain delay us a bit because they close one of the run way so it was not easy to get out"

Pros: "Seats are comfortable, main reason I like this airline. Crew was nice."
Cons: "The screens on the back of the seats are showing their age and the controls on the armrests are causing your neighbor to change your channel or the brightness of the screen. Letting everyone stream content to their own devices would probably be a better option, with safe charging available."

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Cons: "We arrived later for almost 2 hours"

Cons: "The flight did not have enough headphones for in-flight movies. Our tv screens also did not work well."

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

Pros: "Space seating"
Cons: "Same movies going and coming back."

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Cons: "No movies just Direct TV."

Pros: "The comfort of the seats are amazing. I was able to sleep through almost all of the flight."

Pros: "Bring her own earphones as then u can listen to their varied entertainment channels. Gave free snacks & there was quite an assortment so I wasn’t stuck w pretzels again. Free soft drinks; nice flight attendants & smooth ride from Chicago to NY"

Pros: "No gate, waited 2 hours in plane"

Cons: "Passenger behind me was throwing up the whole ride and the steward did nothing about it let it all over the island left the people around them"

Cons: "Late boarding with little communication. Equipment failure delayed the flight after pushing from the gate. Additional delay of 10 mins one we got to the destination gate."

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "The crew was friendly."
Cons: "The boarding policy changes are confusing. No longer boarding from the rear of the plane and no explanation of how to board sooner without buying an extra space seat. Also the seats are less comfortable."

Pros: "Friendly crew"
Cons: "The new boarding group policy is confusing."

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Cons: "flight was delayed 2 hours :("

Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"

Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"

Pros: "Ez check in with kiosk"
Cons: "I would like to see an organic food option, even with a fee if necessary. Recommendation, fruit like banana or apple. Certified organic."

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Entertainment on board"
Cons: "My flights was delayed"

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "Extra leg room"
Cons: "On both legs of our vacation, going and coming we experienced long delays , 2 hours Boston.to Vhicago and 3 hours Chicago to Boston"

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

Cons: "Both ways my flight was significantly delayed. Although Jet Blue sent me notices, none of those came before I was on my way to the airport."

Pros: "L.L Bean crew was amazing!! The tv channels and movies!!"

Pros: "the plane was good!"
Cons: "the plane boarded late"

Pros: "Crew was great. Captain provided lots of updates and provided useful site information prior to landing"
Cons: "TV kept on blacking out"

Pros: "The staff is great, the seats are comfortable, and the food is good"

Pros: "Very helpful customer service, really appreciate their help."
Cons: "I took two JetBlue flights within 4 days, both with delays > 2 hr for mechanical issues. I can count on one hand the number of times I've been significantly delayed in the past 5 years, especially when not in the winter. JetBlue, please fix whatever is wrong with your planes. I've otherwise had nothing but positive experiences with them."

Pros: "Nothing to like. Got to destination 3 hours late each way."
Cons: "No apparent reason for delays except poor planning and inefficiency."

Pros: "Friendly crew, quick boarding, plenty of leg room,free Wi-Fi, free snacks."
Cons: "Seat was slightly uncomfortable at times but that's a very minor complaint. Overall a good experience and would definitely recommend JetBlue to others."

Cons: "Flight never happened. Changed schedule at last minute. Sent a rebooking for a day later but the connecting flight out of Boston stayed the day before. How do you go back in time??"

Pros: "Bag charged"

Cons: "The crew made us move from the seats I booked without a good explanation"

Pros: "There wasn't any in flight entertainment and I didn't order food, so that's why my rating is neutral. Our flight back was 30 min early, so that was great."

Pros: "Crew were arguing with passengers over seating arrangements and when it came time to throw out garbage at the end they completely ignored half of the rows. Even after the lady next to me yelling to get their attention."
Cons: "See above."

Cons: "Lots of screaming children, but I had to fly to Orlando."

Cons: "The seats were uncomfortable, over priced snacks, no foods."

Pros: "On time"
Cons: "All the hidden costs"

Pros: "I will never fly Frontier again. Poor customer service. Poor baggage handling. Poor timeliness of flight and baggage delivery. Poor communication of flight delays and baggage mix-ups. Understaffed. Undertrained. Poor seats, particularly considering I paid for the best. Inadequate compensation for 8+ hour delay and missing baggage for 3 days. After all the nickel and diming for seats, baggage (checked AND carry on) it would have cost me less to fly my preferred carrier and avoided every hassle, not to mention the inadequate compensation (again). Horrible, horrible experience."
Cons: "I will never fly Frontier again. Poor customer service. Poor baggage handling. Poor timeliness of flight and baggage delivery. Poor communication of flight delays and baggage mix-ups. Understaffed. Undertrained. Poor seats, particularly considering I paid for the best. Inadequate compensation for 8+ hour delay and missing baggage for 3 days. After all the nickel and diming for seats, baggage (checked AND carry on) it would have cost me less to fly my preferred carrier and avoided every hassle, not to mention the inadequate compensation (again). Horrible, horrible experience."

Cons: "The onward flight was cancelled and I wasn't provided an immediate alternative flight. On cancelling my entire itinerary, I was charged a cancellation fee and not provided a refund. I would never fly from frontier again."

Pros: "There is almost nothing positive to say about the flight, bounding tolerable."
Cons: "I have flown almost 200 times and this the worst experience I have had. A pathetic display of ineptitude."

Cons: "Where do I begin? Frontier Airlines had us sit in the plane for four hours before cancelling. We pulled away from the gates three times and even deplaned for 15 minutes before they decided to cancel. Just cancel it after a few hours, please. And then when I called Frontier for options, I was told the next available flight was four days away (Jan. 2) and did not offer any other options. Very disappointed in Frontier Airlines. The process of booking through Kayak was good, but I will never fly with Frontier again."

Cons: "all the additional fees, cancels out any savings on fare"

Cons: "My flight was cancelled at the last minute forcing me to look for another flight and ending up buying a very, expensive, last minute ticket on United Airline. I could not accept the flight on December 31, 2015 due to many very important meetings. I hope that this will not happen again."

Cons: "Cancelled...all i got was a refund! No credit voucher or anything for another flight. Not accommodating at all."

Pros: "I've had good luck with a few frontier flights. They're cheaper, and they get you there."
Cons: "If your flight gets cancelled due to weather, they won't work with you. They offered to put me on the next flight - 5 days later. Ridiculous. They offered to get me on another flight the next day - to a different destination - with a $600 up charge per ticket (original ticket price $200). Absurd. Most major airlines get you there the next day, or get you on another airline if they must. Frontier and spirit don't. They'll offer you a refund and tell you to get lost."

Cons: "Had to sit to wait fr long time to get to arrival gate after landing"

Pros: "not much, other than that they got us to where we wanted to go that day!"
Cons: "No TSA- pre-check participation and so it was late! even first bag carry-on is $35 is stupid! plane was late in coming in, and they kept changing times for boarding and we were boarded after 1.5 hours delay and then kept waiting there without moving, then deplaned because of mechanical problems, boarded again after another 1.5 hours delay and then finally left. very bad turbulence and nobody bothered to turn on seat belt sign or warn you or tell you about turbulence, let alone apologize! no food is the norm, but no water, come on! never doing this airline again, even if free!"

Pros: "Nice flight attendants."
Cons: "Pilot apparently didn't have a voice and never once talked to the passengers even when experiencing bad turbulence."

Cons: "screwed by baggage fees"

Pros: "This is in no way a bad relection on Frontier. Kayak sold me the tickets for a certain price and when I started to check in for my flight I had to pay additional for seats and carry on luggage. I ended up paying $102 more for two people on my one way reservation the night before the flight. Kayak should at least make their customers aware that this will happen as it is a lot of money!!!! The flight itself was on time, with a curteous and funny crew. No complains there."

Pros: "Everything went well."

Pros: "Flight was on time"

Pros: "Same as many other reviews, upset I had to pay extra just to select not a premium seat, but literally a seat on a flight I already paid for & pay to either check a bag or carry a bag on. I'll never fly frontier again & probably never book through kayak again either."

Pros: "Boarding was fast"
Cons: "Very very terrible seats. Always late"

Pros: "We had a flight to Philadelphia we boarded on time and landed early! It was great!"

Pros: "The boarding process was really good and the crew was really helpful with helping me with my luggage and finding the seat"
Cons: "The comfort of the plane I couldn't recline my seat the book light didn't work"

Pros: "The staff were very nice."

Pros: "The price was the main reason behind booking. We thought we were getting a great deal on airfare from Chicago to Vegas, and it was a great base fare."
Cons: "The add-ons are where they get you. Pay to check a bag, and then when your bag returns to you demolished (seriously, they broke a wheel off my boyfriend's bag, which has been on many trips via other carriers with no damage, and they tore all the trim off my bag, which i have used for hardcore travel almost monthly). Pay to get decent seating. Pay for refreshments--that's right folks, if you want water on this flight, it'll cost you. Gate agents were huddling, talking to each other while we waited at the front of the line and folks stacked up behind us. Unprofessional. I'm sticking with Southwest from now on. No thanks, frontier."

Pros: "One of the crew members was extremely friendly and helpful."
Cons: "I was not made aware at any point in my booking process that I would be charged for a carry-on, a carry-on?!?! And that the carry-on would cost more than a checked bag. They also charge for water, I mean seriously a cup of water, not a bottled water, just a cup of regular ole' water. You also have to pay additionally for an actual seat assignment on the plane. I will be sure to never book them again! I could have flown with a better carrier for the same price after the nickel-and-dime routine i had to go through with Frontier. On top of everything else, the flight was delayed!"

Pros: "Pay extra for another airlines. Frontier is uncomfortable and you have to pay for everything after the ticket. You only end up saving minimal amounts."

Pros: "Frontier airines was great. We got a ridiculously cheap flight so to pay $30 for a carry on was no problem. We knew all the fees up front so we planned accordingly and packed light. Staff was friendly and organized. Flight got in early."

Cons: "The flight was fine.. We didn't know that we have to pay a luggage fee for a carry on for $45.. I was surprised when they told us to pay since carry on so far in other flights were free.. The seats weren't comfortable since it doesn't recline. This plane really is only good for probably a one hour flight not 4 hours because you can't even relaxed and reclined your seat.. All food you have to pay including water.. I will never fly frontier ever again..."

Pros: "Original ticket price was cheaper than any other, and flight time options were great for an early flight out or late flight in, etc."
Cons: "Cheap and cheap. O'hare has an awful set-up for bag check and security for frontier/spirit/virgin/other cheap airlines together. You wait to print, then wait to check, then wait to drop your own bags (with zero instruction or customer service or signage), then wait for security. They hate for EVERYTHING: just to check in for your flight and pick a seat. $11-17-37 to sit together. Each. And then for bags. $35 to check and $60 to carry on (makes no sense) even when checking in online early. And even more cost to have both checked and carry on. And seats don't recline, that costs more. And have a 4inch by 5 inch-ish tray table. And EVERYTHING costs money onboard from WATER to Pepsi to snacks. It cost an extra $92 each way for two of us to check in and check one small bag. My back hurts and I will ALWAYS pay a bit more for another airline."

Pros: "Nothing"
Cons: "Everything"

Cons: "1) Although flights are fairly low fare, they get you with baggage. Had to pay to check OR to carry-on. 2) Flew out of Chicago O'Hare - a major hub - and Frontier, Spirit, Virgin America, & Alaskan all shared a SINGLE security check. Yes ladies and gentleman, one security scanner. I have never in my life (usually fly American, United, or Southwest) waited more than 30 minutes to get through security. This time was well over an hour, I almost missed my flight. 3) On-board staff was friendly (all but one woman), but there were no complimentary beverages or snacks. I did pay for some & they were not too pricey, but having to whip out my credit card yet again made my whole travel experience feel far from effortless."

Pros: "Staff were very pleasant."
Cons: "Food selection is quite limited."

Pros: "The flight was 40 minutes early!"
Cons: "There is no free food."

Pros: "Really good experience"

Pros: "The price for the trip was great. I thought the boarding was efficient and the flight crew pleasant. Check in at the airport was very easy although the automatic machines were non functing."
Cons: "Long pre security screening lines. The seating is rather cramped."

Pros: "I got where I wanted to go for a reasonable price."
Cons: "I did not calculate for the extra fee for a carry-on. I'm always disappointed when I don't get a complementary beverage and snack. Sad but worth the savings."

Pros: "Flights were cheap."
Cons: "You end up paying an additional $30-35 to check a bag or carry on-board, you also end up paying $15-20 to reserve a seat. In addition, they won't accept your checked-in baggage if you're not at the airport 45 min before boarding to drop it off. They made me re-book my flight out of Chicago for the next day and charged me $99. I was only 5 min late to drop my bag off, and because of bad traffic. The airline has no empathy, they seem to be only concerned with charging you at every opportunity they get. I will never fly frontier again."

Cons: "Frontier airlines. Rigid and unable to admit that they made a mistake. Caution towards anyone who flies with their special low discount rates. Many opportunities were taken by company to recover discounted fare (and I am not referring to any baggage costs) Besides money, they ruined a special weekend through delays. Think twice! In fact, my comment is in reference to customer service in general. Everything is a fight now. I'm not a screamer, I'm rational. I laid out,clearly, where their policy was contradicted and that some empathy was in order and in the process was hung up on once and have not received a reply to my last email. If you gave no intention to achieve quality customer service, why pay for the department? Maybe they don't."

Cons: "It was delayed and arrived 2 hours late. I had booked the flight specifically for its departure and arrival time. It was my first time flying with Frontier, and I will not fly with them again."

Cons: "Lost my luggage and people at check in were rude"

Cons: "Frontier delayed our flight due to a mechanical problem for over twelve hours. Communication was so bad that we could not leave the airport or even the gate because it seemed like we could be leaving at any moment. It got delayed, and delayed and delayed until all the other flights to SFO had left and there was no other option but to pray we got home. Frontier handled the whole situation extremely poorly. I was exhausted and beside myself with frustration. I will never fly Frontier again."

Cons: "inflight everything requires payment."

Cons: "45 dollars for each carry on . Not pleased to pay 90 extra dollars. Never flying Frontier again"

Cons: "While booking I was unaware frontier airlines charged for carry on luggage and didn't participate in TSA pre check. In addition to paying $45 more for the ticket than advertised and having to use normal security, the plane was so cramped the guy behind me hit me in the head. Finally there was a persistent foul smell in the plane. It was a rough 4hrs 30 min. I would recommend spending more and flying southwest or United."

Cons: "The price of the trip did not include a seat, nor baggage, this was unclear and I felt misled. The seating is extremely uncomfortable. Checking in online was terrible, the website was hard to navigate, the prices were inconsistent (I was checking on my phone and computer at the same time and getting different rates for seats). I felt the communication was poor. I did not feel safe. I will not choose this Airline again."

Pros: "Crew and other employees we're curteous. Plane was clean. We trav llhave d before with Frotier and had no problems, until now."
Cons: "It was not pleasing to be delayed 3 times and spend time in the airport instead of being with family and friends. I am thankful that the flight was not cancelled."

Pros: "Crew was very professional, plane was clean. Ride was smooth."
Cons: "I had overweight passenger next to me who tried his very best to keep his left arm away from me, but when he fell asleep I was squeezed. No fault of Spirit. It was too tight of a seat arraignment. When I went to get my seat from customer service there was a man with luggage that will fit the template for carry on, but the wheels did not allow his suitcase to fit the length. He had to pay for his luggage, I thought the representative should have not charge him. I bought my ticket last minute as it was business trip decided 2 days prior. I chose Spirit for the convenient schedule, never used them before. For the same amount of money a coworker of mine got very convenient flight with no charge for carry on with assigned seats with American. I thinkg the price was not competitive."

Pros: "The isle seat, the price, tsa"
Cons: "Had a great trip."

Cons: "The aircraft was freezing. The water was not complementary and I didn’t have a card to pay with I only had cash. The seat was extremely hard and uncomfortable. The flight was last taking off and landing."

Pros: "Flight was on time"
Cons: "Food we did pay for snack It was more expensive, I'll rather fligh with an airline that tell me up fron how much I will expend on my ticket instead o giving me a low price and then charge me for everything."

Cons: "Good"

Cons: "Departing and landing was great I will fly again and again"

Cons: "The plan was dirty. They need to make sure they wipe down everything. It gross"

Cons: "them charging for everything except the bathroom"

Pros: "The crew was nice overall. You can have coffee raffles for free. Seats weren't too bad for 5 hours flights."
Cons: "The Microphones were too loud. the crew talked too much trying to sell the rewards card. It was frustrating that the carry on is too expensive. I paid $100 total for my carry on. I thought I was saving money using this airline but I end up paying more for fewer services. My flight was 5 house flight with no wifi service. nothing to entertain with. I don't think I would take this airline again unless its 1-hour flight with no carry-on."

Cons: "Double booking of seats"

Cons: "I was running late for my flight and the charged me for a whole new flight."

Pros: "I selected my seat when I checked in and to my surprise, I had the entire row to myself. This was great cause I'm a bigger girl and the seats are VERY close together and small. I actually felt bad for the other passengers that were crammed in like sardines."
Cons: "I really had no complaints that could be corrected... turbulence was pretty bad but with the weather conditions, that was to be expected."

Pros: "Landed early and gate open. Great trip all over he way even though in a middle seat"

Pros: "nothing"
Cons: "flight was delayed seat was terrible terrible airline"

Cons: "Paying for every single carry on suitcase"

Pros: "We boarded quickly and efficiently. We arrived at our final destination early."
Cons: "Seats were not very comfortable, but the flight was short so it did not matter too much."

Pros: "About the only thing that I can say I liked is, the boarding process went smothly for me & my luggage was on time."
Cons: "Where to start... paid more in bag fees & to get an isle seat for each(4)flights than I did for damn plane ticket! Flights delayed 4hrs another flight in same trip delayed 2 hours. Staff wasn't interactive/friendly I'd say 6/10 were nice. Asked for an isle seat the person helping at counter, said I'd have to pay to upgrade. Seriously- upgrade for isle seat!! I paid to have an isle seat on all 4 flights(I'm a disabled vet who was injured in the line of duty) I need easy access to toilets I'm unable to crawl over people, in turn need idle seat). Paid for isle seat all 4 flights- just to see the flights were super empty, people were sitting where they wanted anyway. Thanks for taking my $ for the seats tho spirit:-|. Staff wasn't that friendly compared to other airlines I've flown on. Not food. No entertainment on flight. Not worth it. If they don't do better business they won't last long I feel. There is potential just needs some work!"

Cons: "Crew food boarding check in employ not profesional"

Cons: "Same as above."

Pros: "low fare"
Cons: "check in process was confusing- one airport you had to pre-print, the other you didn't, no cell phone tickets allowed. There are higher fees for carry-ons than checked bags. Didn't like the attitude/marketing at all. I've flown other no-frills carriers but these guys just rubbed me the wrong way!"

Pros: "The tight quarters were challenging for my near 6 ft son. However, because the seats don't recline, he didn't loose any room to the person in front of him."
Cons: "Very few snack choices to purchase for anyone who is gluten-free ."

Cons: "I had a connecting flight form San Jose to Chicago in Fort Lauderdale. Both Flights were Spirit. Had around 2 yrs to get from my flight from San Jose to the chocago flight. By the time i went thru customs (huge line) then thru security (another huge line) i got the the gate at 7:38 A. M. My flight was scheduled to leave at 7:42 A.M.. I understand that you do need to close your gates a little earlier, but i was not the only one that had the same itenerary and missed the flight. Its just hard to understand that you must have a record of who is missing on that flight and since you know they are at the airport (because we came in from San Jose on your flight) not to at least wait until 7:42 to close the gates. There was no one at the gate, the gate was closed as we watched the airplane sit there without moving for at least another 10 minutes. Its beyond logic and the only way i can explain that in my mind is that your record of competing with other airlines of being on time is more important to the airline than the customers themselves. Which is very sad. Then i stood in line for one and a half hours just so i can speak to someone on what my next step should be. Do you have any idea how stressful it is to miss your flight and then have to stay in line for another hour and a half in that stress? As i stood there and watched the couple in front of me being in distress and his girlfriend crying i realized how unfriendly Spirit Airlines is ti its cutomers. Then finally i get to the representitve to be told i can get a flight out at 6:15 P.M. That is 10 and half hours later. So i inquired, can we use another airline or even an alternative airport to resolve the long wait, of course i was told no without any explanation. So, i had my office search for a flight for me and they found one for 101.00 to Midway with Southwest Airlines leaving at 10:15 A.M., but since i was in a different terminal and would have to go thru security, i would not make it. Very frustrating to think since your air line is the one that propsed the itenerary for me, would not back me up when i missed the flight with no fault of mine. Afterall, Spirit sold me that Itenerary, they should have been aware that it can take longer than two hours to make it to the next flight. But, what really has me steaming is you could not even have more than one person to help at the counter for the people that missed their flight, because if you DID then i could have had time to book the Southwest flight. Due to your lack of concern about the customers in general my company nor I will ever use your services again. I know that probably doesnt break your heart, but me being in business now for well over 30 years,i can gaurantee you eventually if you do not change your practices, it will affect your bottom line. One last note. I overheard another frustrated customer asking if they will give him any food vouchers, and he was stared down for a few seconds and then a simple "no"."

Pros: "Seats were comfortable"
Cons: "It is absurd to charge 55 bucks for a carry on!! Also ridiculous there is no beverage service"

Pros: "The boarding process was quick and organized both ways."
Cons: "On the flight in to ft. Myers, the flight attendants were all grumpy and unfriendly. The seats are entirely too small - I am an average-sized female and felt very crammed into the seat area. At one point, I dropped something but there wasn't even enough room for me to bend down and get it - I had to kick it over and ask the smaller person next to me to pick it up for me! I thought I would have an anxiety attack in such a small space. I will never fly Spirit again."

Cons: "I flew in/out of two major cities and was reluctant to fly on Spirit, for good reason. Flight information was difficult to find at airport (Spirit rented a United gate and did not have any listed information on boards) and I relied entirely on my phone to follow flight delays and changes. When flight was cancelled there was no effort accomodate passengers on another airline, despite many flights available, and the next Spirit flight was two days later!!! Spirit offered refunds for that flight but the website did not work for two days and the wait was very long, over 20 minutes, on the phone. The baggage and seat fees add a significant amount to the cost of the ticket so that it is no longer less expensive than a more reliable airline. I will never fly Spirit again."

Cons: "Cancelled my flight at the last second."

Cons: "I was charged an extra $50 to check-in my bag at the counter! Quite mean! I wasn't preinformed!"

Pros: "The flight was good. I wish there had been a little more room but I will definitely fuse Spirit again if the flight is the right price"

Pros: "Seats looked new"
Cons: "The flight was delayed over an hour & half due to 'no landing time in NY'. Totally unrelated to weather or the aircraft. Drinks are available for a fee - even water!"

Cons: "You lie about the real price of the flight. $45 for a carry on? one way?!? Thought this was America. Thanks, Obama."

Pros: "Spirit cancelled my flight never again will I use this service made me lose lots of money and lost out on my brother's wedding"

Pros: "Staff was all very nice."
Cons: "The aisle that had passengers sit in who had to verbally agree to aid getting door open had a drunk man who agreed. He never should have sat in that aisle."

Cons: "Try getting charged for your bags only to then get stuck paying even more for your seats because the only ones left. The last available seats where in an exit row and I was forced either to pay extra to check my bags in at the airport or choose and pay for the last available seats. Either way they squeezed every last penny out of us."

Pros: "Nothing."
Cons: "i had to pay my on board luggage, the chair doesn't reclinate, no food, no intertainment and the price was not that cheap to justify all of these down sides"

Cons: "I DON'T WANT ANY FLIGHT CREDITS."

Pros: "Quick boarding. Do not like the pay more for larger seat or exit row. Flight was uneventful. Staff on board very pleasant."
Cons: "See above"

Cons: "The plane took off about a half hour late because they switched our gate at the time we were supposed to start boarding. Everyone had to be moved from one end of the terminal to the other."

Cons: "Very unsophisticated passengers"

Pros: "On time."

Pros: "The best part of my flight to Atlanta was the price. The service for this leg from checking in through landing was excellent. The seats were pretty comfortable (although I'm not sure they reclined - couldn't see how they would), flight attendants friendly and capable, and I appreciated the announcement re where to find our checked bags."
Cons: "I didn't order coffee during this leg, having ordered it on my trip out and finding that it tasted like instant machine coffee.... I had an aisle seat, and the mother and young son next to me talked loudly during the entire flight, making it hard to concentrate in my reading in spite of wearing earplugs. But this has nothing to do with Spirit - simply their ignorance and lack of consideration and my being unwilling to speak with them about it."

Pros: "Nothing at all. Worst experience ever in 34 years of travelling."
Cons: "First answer is selfexplanatory!"

Pros: "Landed Safely"
Cons: "Seats were cramped. Had to streatch out legs and couldn't. Gentleman next to me was 6ft 6inches and was visibly uncomfortable."

Pros: "The only thing to like about my flight was Spirit was the cost of the flight availability, but in evaluation the cost just isn't worth it"
Cons: "Spirit does not participate in TSA Pre check, which wasn't communicated during my purchase, which caused me to almost miss my flight due to security. You are required to pay for drinks and food, but the quality is sub par and not worth the price. Seats do not recline , which is not great for a flight longer than two hours."

Cons: "there is no free luggage. the luggage fee even more than the ticket."

Pros: "-In general with Spirit you know what you're getting. A cheap flight with only the bare bone necessities to get you where you're going. Generally I'm okay with this approach to save a buck or two but this experience tipped me over the edge of never flying Spirit again."
Cons: "To paint a picture before I get into details, public transit broke down so there was a huge rush of passengers for this flight and others, all leaving around the same time of night as the last round of flights from the airport. -The man at the counter said he could not print our boarding passes because the flight was already boarding as it was 30 minutes before doors closed. -We used the terminal and got an error message saying to see someone at the counter, so we went back and talked to another lady at the Spirit counter. She printed our tickets and was even able to check in my last minute checked bag. -No one at Spirit would walk us through security, which I guess is understandable (though a common courtesy on other airlines) when the security line was so long. -By this time the security line was so long after we had fumbled around for 10 extra minutes with the first man at the Spirit counter that we decided to give up. We later found out that they held the doors for 15 minutes because of the long lines at security, information which no one at Spirit ever volunteered for us, which would've allowed us to get on the plane. -There were 3 or 4 other passengers very upset at the counter employees not willing to print their boarding passes for them who could have also made the plane. -We had to get a flight out the next morning to make our international flight from BWI, so we wanted to go get the checked bag back from Spirit. This was by far the best part of the trip, as the woman at baggage was able to confirm my bag had made it on the flight and would be landing in Philadelphia. -To confirm the bag landed and we would be able to pick it up at 9am when our flight landed the next morning, we called the Spirit office at the Philly airport. The woman said to call back at 12:30-12:45 and she would let us know if she had the bag. This was important for us, because if my bag wasn't there I could just pack another for our international trip and deal with finding the lost bag at a later time. -We called 8 times between 12:30 and 1:30 with no response. We also left several voicemails. -At 5am on our way back to O'Hare we were again unable to get ahold of anyone at Spirit in Philadelphia. While boarding our flight to Philly we finally got a hold of someone who said they would go check the office and let us know within 10 minutes. Obviously too late for me to pack another bag, but at least we could plan over the next several hours. Never got a call back, and only received voice mail after attempting contact again several times as our plane prepared for takeoff. -Landed in Philly and what do you know, the Spirit office is closed for most hours of the day, only operating around their scheduled flights. The info. employee at the airport wished us good luck in a hopeless tone. After 45 minutes of panic calling every Spirit phone number we could find, we finally got someone on the phone to come get my bag out of the locked office."

Pros: "New euipment."
Cons: "Final cost was deceiving."

Pros: "Flight cancelled twice on two separate days. Little compassion by the staff. Waiting room at O'hare was filthy, seats ripped with stuffing hanging outl. The discounted price is not worth the inconsistent and terrible service. Eventually rescheduled with another airline."

Pros: "The crew was nice!"
Cons: "I had NO IDEA bringing the bag as a carryon was an additional $55 each way. I could have bought a ticket on a better airline for cheaper if I had known. Also, no wifi at all (even for sale) and you can't even get a glass of water without paying for it. Then they push the Spirit airlines credit card on you. Tacky. Awful."

Pros: "The trip was good I think they did the Best"

Cons: "I don't like that they allow people with carry-ons larger than the specified sizes. I was careful to follow the guidelines, which were hard to find anyway. I don't like the credit card sales pitch on each flight."

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Chicago O'Hare Intl to Caribbean Islands

Airlines flying from Chicago O'Hare Intl to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Chicago O'Hare Airport to Caribbean Islands

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12/16
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13h 09m
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14h 34m
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26h 30m
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